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Novel mch receptor antagonists

a technology of mch receptor and antagonist, which is applied in the field of medicine, can solve the problems of economic and social costs, excess body fat, and excess weigh

Inactive Publication Date: 2006-03-09
ELI LILLY & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention relates to a new compound, its pharmaceutically acceptable salt, solvate, enantiomer, mixture of diastereomers, or prodrug. The compound has a specific structure and can be used to treat various medical conditions. The invention also provides methods for making the compound and its various forms. The technical effect of the invention is to provide a new compound with improved efficacy and safety for the treatment of medical conditions.

Problems solved by technology

The affluence of the 90's along with the exponential increase in food production particularly in Western and Asian economies has resulted in feeding patterns that lead to obesity.
Excessive weight is generally characterized by excessive body fat, because unused energy is stored in the adipose tissues as fat.
Obesity has associated with it, economic and social costs.
Moreover, obese persons are more likely to have medical problems associated with or exacerbated by the excess body weight.
Patient compliance, however, is usually poor.
The problem is compounded by the fact that there are currently only two medications approved for the treatment of obesity (sibutramine, or Meridia™ and orlistat, or Xenical™.
Current treatments targeted at obesity have side effects.
These agents have not been proven effective for all patients and for sustainable periods of time.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

formulation examples

Formulation 1

Tablets

[0214]

IngredientQuantity (mg / tablet)Active Ingredient 5-500Cellulose, microcrystalline200-650Silicon dioxide, fumed 10-650Stearate acid 5-15

[0215] The components are blended and compressed to form tablets.

Formulation 2

Suspensions

[0216]

QuantityIngredient(mg / 5 ml)Active Ingredient5-500mgSodium carboxymethyl cellulose50mgSyrup1.25mgBenzoic acid solution0.10mlFlavorq.v.Colorq.v.Purified water to5ml

[0217] The medicament is passed through a No. 45 mesh U.S. sieve (approximately 355 micron opening) and mixed with the sodium carboxymethyl cellulose and syrup to form a smooth paste. The benzoic acid solution, flavor, and color are diluted with some of the water and added, with stirring. Sufficient water is then added to produce the required volume.

Formulation 3

Intravenous Solution

[0218]

IngredientQuantityActive Ingredient25mgIsotonic saline1,000ml

[0219] The solution of the above ingredients is intravenously administered to a patient at a rate of about 1 ml per minu...

example 1

Preparation of 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(3-dimethylamino-propyl)-amide oxalate

[0270]

[0271] A solution of 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (0.91 g, 2.5 mmol, 1 eq.) in anhydrous THF (10 mL) was treated with 1,1′-carbonyldiimidazole (0.41 g, 2.55 mmol, 1.02 eq.) and the resulting solution heated to 60° C. for 25 minutes.

[0272] The solution was then allowed to cool and the 3-(dimethylamino)propylamine (0.31 g, 0.38 mL, 3 mmol, 1.2 eq.) was added via syringe. The reaction was allowed to stir at room temperature.

[0273] After 2 hours, the reaction was diluted with water and extracted with 2×150 mL EtOAc. The organic layers were combined, dried over MgSO4, filtered, and the solvent removed in vacuo leaving 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (3-dimethylamino-propyl)-amide (0.97 g, 87% yield) as a yellow oil.

[0274] Dissolved 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(3-dimethyla...

example 2

Preparation of 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (2-dimethylamino-ethyl)-amide oxalate

[0276]

[0277] Prepared in the same manner as described for example 1. A solution of 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(0.68 g, 1.87 mmol, 1 eq.) was treated with 1,1′-carbonyldiimidazole (0.31 g, 1.91 mmol, 1.02 eq.) and warmed as described. The reaction was allowed to cool and then treated with N′,N-dimethylethylenediamine (0.20 g, 2.24 mmol, 1.2 eq.). The reaction was treated as described in example 1 to give 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid(2-dimethylamino-ethyl)-amide (0.76 g, 94% yield) as a faint yellow oil.

[0278] The free base was converted to the oxalate salt as described in example 1 using 0.20 g of oxalic acid giving 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid (2-dimethylamino-ethyl)-amide oxalate (0.5584 g) as a white solid.

[0279]1H NMR (DMSO-d6) δ 8.89 (br, 1H), 8.14 (s, 1H), 7.84-7.2...

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Abstract

The present invention relates to a melanin concentrating hormone antagonist compound of Formula I: (I) wherein Ar1, Ar2, Ar3, L1, L2 and Q areas defined, or a pharmaceutically acceptable salt, solvate, enantiomer or mixture of diastereomers thereof useful in the treatment, prevention or amelioration of symptoms associated with obesity and Related Diseases.

Description

FIELD OF THE INVENTION [0001] The present invention is in the field of medicine, particularly in the treatment of obesity and diseases caused by or exacerbated by obesity. More specifically, the present invention relates to antagonists of melanin concentrating hormone useful in the prevention and / or treatment of obesity and related diseases. BACKGROUND OF THE INVENTION [0002] The affluence of the 90's along with the exponential increase in food production particularly in Western and Asian economies has resulted in feeding patterns that lead to obesity. Obesity is defined as being excessively overweight. Excessive weight is generally characterized by excessive body fat, because unused energy is stored in the adipose tissues as fat. [0003] Obesity has associated with it, economic and social costs. Obese people, an increasing proportion of most western societies, are regarded as having out of control feeding habits often associated with low self-esteem. Moreover, obese persons are more...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/205C07C323/39A61P3/04C07C323/60
CPCC07C323/60A61P1/04A61P11/00A61P11/06A61P13/08A61P13/10A61P25/24A61P27/02A61P27/06A61P3/04A61P43/00A61P9/00A61P3/10
Inventor GILLIG, JAMES RONALDHEINZ, LAWRENCE JOSEPHKINNICK, MICHAEL DEANLAI, YEN-SHIMORIN, JOHN MICHAELSNYDER, NANCY JUNE
Owner ELI LILLY & CO
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